Substituted phenylketoenols and their use as pesticides and herbicides

ABSTRACT

The invention relates to novel phenyl-substituted cyclic ketoenols of the formula (I)                    
     in which 
     Het represents one of the groups                    
      and G, V, W, X, Y and Z are each as defined in the description, 
     to processes and intermediates for their preparation and to their use as pesticides and herbicides.

This application is a 371 of PCT/EP97/06708 filed Dec. 1,1997.

TECHNICAL FIELD OF THE INVENTION

The invention relates to novel phenyl-substituted cyclic ketoenols, to aplurality of processes and intermediates for their preparation and totheir use as pesticides and herbicides.

BACKGROUND OF THE INVENTION

It is already known that certain phenyl-substituted cyclic ketoenols areactive as insecticides, acaricides and/or herbicides.

1H-arylpyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334,EP-A-596 298, EP-A-613 884, EP-A-613 885, DE 44 40 594, WO 94/01 997, WO95/01 358, WO 95/20 572, EP-A-668 267, WO 95/26 954, WO 96/25395 and WO96/35 664) having insecticidal, acaricidal and in some cases herbicidalactivity are known.

It is known that certain substituted Δ³-dihydrofuran-2-one-derivativeshave herbicidal properties (cf. DE-A-4 014 420). The synthesis of thetetronic acid derivatives (such as, for example,3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-Δ³-dihydrofuran-(2)-one)used as starting materials is also described in DE-A-4 014 420.Compounds of a similar structure are known from the publication Campbellet al., J. Chem. Soc., Perkin Trans. 1, 1985, (8) 1567-76, without aninsecticidal and/or acaricidal activity being mentioned. Furthermore,3-aryl-Δ³-dihydrofuranone derivatives having herbicidal, acaricidal andinsecticidal properties are known from EP-A-528 156, EP-A-0 647 637, WO96/25395, WO 96/20196 and the abovementioned hitherto undisclosed patentapplication. 3-aryl-Δ³-dihydrothiophene-one derivatives are also known(WO 95/26 345, WO 96/25395 and WO 96/35664).

However, the acaricidal and insecticidal activity and/or spectrum ofactivity and/or plant tolerance of these compounds, in particular withrespect to crop plants, is not always satisfactory.

DETAILED DESCRIPTION OF THE INVENTION

The invention, accordingly, provides novel compounds of the formula (I)

in which

V represents hydrogen, halogen, alkyl or alkoxy,

W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkinyl,alkoxy, halogenoalkyl, halogenoalkoxy or in each case optionallysubstituted phenyl, phenoxy, phenylthio, phenylalkoxy orphenylalkylthio,

X represents halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano, nitro or in each case optionally substitutedphenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,

Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro,

Z represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, hydroxyl, cyano, nitro or in each case optionallysubstituted phenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or

Y and Z together with the linking carbon atoms represent an optionallysubstituted cycle which is optionally interrupted by one or moreheteroatoms, or

W and Z together with the linking carbon atoms represent an optionallysubstituted cycle which is optionally interrupted by one or moreheteroatoms,

Het represents one of the groups

in which

G represents hydrogen (a) or represents one of the groups

in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R¹ represents in each case optionally halogen- or cyano-substitutedalkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl orrepresents in each case optionally halogen-, alkyl- oralkoxy-substituted cycloalkyl or heterocyclyl or represents in each caseoptionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl,

R² represents in each case optionally halogen- or cyano-substitutedalkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents in eachcase optionally substituted cycloalkyl, phenyl or benzyl,

R³, R⁴ and R⁵ independently of one another each represent in each caseoptionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino,alkylthio, alkenylthio or cycloalkylthio or represent in each caseoptionally substituted phenyl, benzyl, phenoxy or phenylthio,

R⁶ and R⁷ independently of one another each represent hydrogen,represent in each case optionally halogen- or cyano-substituted alkyl,cycloalkyl, alkenyl, alkoxy, alkoxyalkyl or represent in each caseoptionally substituted phenyl or benzyl, or together with the linking Natom form an optionally oxygen- or sulphur-containing and optionallysubstituted cycle.

The compounds of the formula (I) can be present, depending, inter alia,on the nature of the substituents, as optical isomers or isomer mixturesof differing composition which, if appropriate, can be separated in acustomary manner. Both the pure isomers and the isomer mixtures, theirpreparation and use, and compositions comprising them are part of thesubject matter of the present invention. In the following, forsimplicity, however, compounds of the formula (I) are always referredto, although pure compounds and, if appropriate, mixtures havingdifferent proportions of isomeric compounds are intended.

Including the meanings (1) to (3) of the group Het, the followingprincipal structures (I-1) to (I-3) result:

in which

G, V, W, X, Y and Z are each as defined above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-1-a) to (I-1-g)result if Het represents the group (1)

in which

E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-2-a) to (I-2-g)result if Het represents the group (2)

in which

E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-3-a) to (I-3-g)result if Het represents the group (3)

in which

E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by the processes described below:

(A) compounds of the formula (I-1-a)

in which

V, W, X, Y and Z are as defined above

are obtained when

compounds of the formula (II)

in which

V, W, X, Y and Z are each as defined above

and

R⁸ represents alkyl (preferably C₁-C₆-alkyl)

are intramolecularly condensed in the presence of a diluent and in thepresence of a base.

(B) Moreover, it has been found that compounds of the formula (I-2-a)

in which

V, W, X, Y and Z are each as defined above

are obtained when

compounds of the formula (III)

in which

V, W, X, Y, Z and R⁸ are each as defined above

are intramolecularly condensed in the presence of a diluent and in thepresence of a base.

(C) Furthermore, it has been found that compounds of the formula (I-3-a)

in which

V, W, X, Y and Z are each as defined above

are obtained when

compounds of the formula (IV)

in which

V, W, X, Y, Z and R⁸ are each as defined above and

T represents hydrogen, halogen, alkyl (preferably C₁-C₆-alkyl) or alkoxy(preferably C₁-C₈-alkoxy)

are intramolecularly cyclized, if appropriate in the presence of adiluent and in the presence of an acid.

Moreover, it has been found

(D) that the compounds of the formulae (I-1-b) to (I-3-b) shown above inwhich R¹, V, W, X, Y and Z are each as defined above are obtained whencompounds of the formulae (I-1-a) to (I-3-a) shown above in which V, W,X, Y and Z are each as defined above are in each case reacted

α) with acyl halides of the formula (V)

in which

R¹ is as defined above and

Hal represents halogen (in particular chlorine or bromine)

or

β) with carboxylic anhydrides of the formula (VI)

R¹—CO—O—CO—R¹  (VI)

in which

R¹ is as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder;

(E) that the compounds of the formulae (I-1-c) to (I-3-c) shown above inwhich R², V, W, M, X, Y and Z are each as defined above and L representsoxygen are obtained when compounds of the formulae (I-1-a) to (I-3-a)shown above in which V, W, X, Y and Z are each as defined above are ineach case reacted

with chloroformic esters or chloroformic thioesters of the formula (VII)

R²—M—CO—Cl  (VII)

in which

R² and M are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder;

(F) that compounds of the formulae (I-1-c) to (I-3-c) shown above inwhich R², V, W, M, X, Y and Z are each as defined above and L representssulphur are obtained when compounds of the formulae (I-1-a) to (I-3-a)shown above in which V, W, X, Y and Z are each as defined above are ineach case reacted

with chloromonothioformic esters or chlorodithioformnic esters of theformula (VIII)

in which

M and R² are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(G) that compounds of the formulae (I-1-d) to (I-3-d) shown above inwhich R³, V, W, X, Y and Z are each as defined above are obtained whencompounds of the formulae (I-1-a) to (I-3-a) shown above in which V, W,X, Y and Z are each as defined above are in each case reacted

with sulphonyl chlorides of the formula (IX)

R³—SO₂—Cl  (IX)

in which

R³ is as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(H) that compounds of the formulae (I-1-e) to (I-3-e) shown above inwhich L, R⁴, R⁵, V, W, X, Y and Z are each as defined above are obtainedwhen compounds of the formulae (I-1-a) to (I-3-a) shown above in whichV, W, X, Y and Z are each as defined above are in each case reacted

with phosphorus compounds of the formula (X)

in which

L, R⁴ and R⁵ are each as defined above and

Hal represents halogen (in particular chlorine or bromine),

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(I) that compounds of the formulae (I-1-f) to (I-3-f) shown above inwhich E, V, W, X, Y and Z are each as defined above are obtained whencompounds of the formulae (I-1-a) to (I-3-a) in which V, W, X, Y and Zare each as defined above are in each case reacted

with metal compounds or amines of the formuale (XI) or (XII)

Me(OR¹⁰)₁  (XI)

in which

Me represents a mono- or divalent metal (preferably an alkali metal oralkaline earth metal, such as lithium, sodium, potassium, magnesium orcalcium),

t represents the number 1 or 2 and

R¹⁰, R¹¹, R¹² independently of one another each represent hydrogen oralkyl (preferably C₁-C₈-alkyl),

if appropriate in the presence of a diluent,

(J) that compounds of the formulae (I-1-g) to (I-3-g) shown above inwhich L, R⁶, R⁷, V, W, X, Y and Z are each as defined above are obtainedwhen compounds of the formulae (I-1-a) to (I-3-a) shown above in whichV, W, X, Y and Z are each as defined above are in each case reacted

α) with isocyanates or isothiocyanates of the formula (XIII)

R⁶—N═C═L  (XIII)

in which

R⁶ and L are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst or

β) with carbamoyl chlorides or thiocarbamoyl chlorides of the formula(XIV)

in which

L, R⁶ and R⁷ are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Furthermore, it has been found that the novel compounds of the formula(I) have very good activity as pesticides, preferably as insecticides,acaricides and herbicides, and that they are additionally frequentlyvery well tolerated by plants, in particular by crop plants.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents and/or ranges of the radicalslisted in the formulae mentioned herein above and herein below areillustrated below:

V preferably represents hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy,

W preferably represents hydrogen, nitro, cyano, halogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy or preferably represents in each case optionallyhalogen-, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, nitro- or cyano-substituted phenyl, phenoxy,phenylthio, phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio,

X preferably represents halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano, nitro or preferably represents in each case optionally halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,nitro- or cyano-substituted phenyl, phenoxy, phenylthio,phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio.

Y preferably represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

Z preferably represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, hydroxy, cyano, nitro orpreferably represents in each case optionally halogen, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro- orcyano-substituted phenoxy, phenylthio, thiazolyloxy, pyridinyloxy,pyrimidyloxy, pyrazolyloxy, phenyl-C₁-C₄-alkyloxy orphenyl-C₁-C₄-alkylthio or

Y and Z together with the linking carbon atoms preferably represent ineach case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy- orC₁-C₄-halogenoalkyl-substituted C₃-C₅-alkanediyl or C₃-C₅-alkenediyl inwhich optionally one to three members may be replaced independently ofone another by oxygen, sulphur, nitrogen or a carbonyl group, or

W and Z together with the linking carbon atoms preferably represent ineach case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy- orC₁-C₄-halogenoalkyl-substituted C₃-C₅-alkanediyl or C₃-C₅-alkenediyl inwhich one to three members may be replaced independently of one anotherby oxygen, sulphur, nitrogen or a carbonyl group.

Het preferably represents one of the groups

G preferably represents hydrogen (a) or preferably represents one of thegroups

(in particular represents (a), (b) or (c))

in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ preferably represents in each case optionally halogen- orcyano-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl or preferably represents optionallyhalogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur,

preferably represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulfonyl-substituted phenyl, preferablyrepresents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl,

represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryl having one or two heteroatoms from the groupconsisting of oxygen, sulphur and nitrogen, for example pyrazolyl,thiazolyl, pyridyl, primidyl, furamyl or thienyl,

preferably represents optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl or

preferably represents optionally halogen-, amino- orC₁-C₆-alkyl-substituted 5-or 6-membered hetaryloxy-C₁-C₆-alkyl havingone or two heteroatoms from the group consisting of oxygen, sulphur andnitrogen, for example pyridyloxy-C₁-C₆-alkyl, pyrimidyl-C₁-C₆-alkyl orthiazolyloxy-C₁-C₆-alkyl).

R² preferably represents in each case optionally halogen- orcyano-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkylor poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,

preferably represents optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or

preferably represents in each case optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl.

R³ preferably represents optionally halogen-substituted C₁-C₈-alkyl orpreferably represents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano- ornitro-substituted phenyl or benzyl.

R⁴ and R⁵ independently of one another each preferably represent in eachcase optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio orC₃-C₈-alkenylthio or preferably represent in each case optionallyhalogen-, nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-,C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-, C₁-C₄-alkyl- orC₁-C₄-halogenoalkyl-substituted phenyl, phenoxy or phenylthio.

R⁶ and R⁷ independently of one another each preferably representhydrogen, preferably represent in each case optionally halogen- orcyano-substituted C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy,C₃-C₈-alkenyl or C₁-C₈-alkoxy-C₂-C₈-alkyl, preferably represent in eachcase optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl orC₁-C₈-alkoxy-substituted phenyl or benzyl or together preferablyrepresent an optionally C₁-C₆-alkyl-substituted C₃-C₆-alkylene radicalin which optionally one methylene group is replaced by oxygen orsulphur.

V particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl or C₁-C₄-alkoxy.

W particularly preferably represents hydrogen, nitro, cyano, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy or particularly preferably represents in each caseoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenoxy or benzyloxy.

X particularly preferably represents fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano, nitro or particularly preferably represents in each caseoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenoxy or benzyloxy.

Y particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro.

Z particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, hydroxyl, cyano, nitro or particularly preferablyrepresents in each case optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenoxy or benzyloxyor

Y and Z together with the linking carbon atoms particularly preferablyrepresent in each case optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy- or C₁-C2-halogenoalkyl-substitutedC₃-C₄-alkanediyl or C₃-C₄-alkenediyl in which optionally one or two notdirectly adjacent members may be replaced independently of one anotherby oxygen, sulphur or nitrogen, or

W and Z together with the linking carbon atoms particularly preferablyrepresent in each case optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy- or C₁-C₂-halogenoalkyl-substitutedC₃-C₄-alkanediyl or C₃-C₄-alkenediyl in which one or two not directlyadjacent members may be replaced independently of one another by oxygen,sulphur or nitrogen.

Het particularly preferably represents one of the groups

G particularly preferably represents hydrogen (a) or particularlypreferably represents one of the groups

(in particular represents (a), (b) or (c))

in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ particularly preferably represents in each case optionally fluorine-or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₁-C₆-alkyl or particularly preferably representsoptionally fluorine-, chlorine-, C₁-C₅-alkyl- orC₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally one or twonot directly adjacent methylene groups are replaced by oxgyen and/orsulphur,

particularly preferably represents optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₃-halogenoalkyl-, C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl,

particularly preferably represents optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl- orC₁-C₃-halogenoalkoxy-substituted phenyl-C₁-C₄-alkyl,

particularly preferably represents in each case optionally fluorine-,chlorine-, bromine- or C₁-C₄-alkyl-substituted pyrazolyl, thiazolyl,pyridyl, pyrimidyl, furanyl or thienyl,

particularly preferably represents optionally fluorine-, chlorine-,bromine- or C₁-C₄-alkyl-substituted phenoxy-C₁-C₅-alkyl or

particularly preferably represents in each case optionally fluorine-,chlorine-, bromine-, amino- or C₁-C₄-alkyl-substitutedpyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkyl orthiazolyloxy-C₁-C₅-alkyl.

R² particularly preferably represents in each case optionally fluorine-or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl,

particularly preferably represents optionally fluorine-, chlorine-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or

particularly preferably represents in each case optionally fluorine-,chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₃-alkoxy-,C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substituted phenyl orbenzyl.

R³ particularly preferably represents optionally fluorine- orchlorine-substituted C₁-C₆-alkyl or particularly preferably representsin each case optionally fluorine-, chlorine-, brornine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-, C₁-C₂-halogenoalkoxy-, C₁-C₂-halogenoalkyl-, cyano- ornitro-substituted phenyl or benzyl.

R⁴ and R⁵ independently of one another each particularly preferablyrepresent in each case optionally fluorine- or chlorine-substitutedC₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino,C₁-C₆-alkylthio or C₃-C₄-alkenylthio or particularly preferablyrepresent in each case optionally fluorine-, chlorine-, bromine-,nitro-, cyano-, C₁-C₃-alkoxy-, C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-,C₁-C₃-halogenoalkylthio-, C₁-C₃-alkyl or C₁-C₃-halogenoalkyl-substitutedphenyl, phenoxy or phenylthio.

R⁶ and R⁷ independently of one another each particularly preferablyrepresent hydrogen, particularly preferably represent in each caseoptionally fluorine-, or chlorine-substituted C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl, particularly preferably represent in each caseoptionally fluorine-, chlorine-, brornine-,C₁-C₅-halogenoalkyl-,C₁-C₅-alkyl- or C₁-C₅-alkoxy-substituted phenyl orbenzyl, or together particularly preferably represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onemethylene group is replaced by oxygen or sulphur.

V very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, propyl, iso-propyl, tert-butyl, methoxy, ethoxy,propoxy or iso-propoxy.

W very particularly preferably represents hydrogen, nitro, cyano,fluorine, chlorine, bromine, methyl, ethyl, propyl, n-butyl, iso-propyl,iso-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, phenyl or benzyloxy.

X very particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, propyl, butyl, iso-butyl, iso-propyl, methoxy, ethoxy,propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano, nitro, phenyl or benzyloxy.

Y very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl,tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano or nitro.

Z very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, propyl, butyl, iso-butyl, iso-propyl,tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano or nitro or

Y and Z together with the linking carbon atoms very particularlypreferably represent optionally fluorine-, chlorine-, methyl-, ethyl-,propyl-, iso-propyl-, methoxy-, ethoxy-, propoxy-, iso-propoxy- ortrifluoromethyl-substituted C₃-C₄-alkanediyl in which optionally two notdirectly adjacent members are replaced by oxygen or

W and Z together with the linking carbon atoms very particularlypreferably represent optionally fluorine-, chlorine-, methyl-, ethyl-,propyl-, iso-propyl-, methoxy-, ethoxy-, propoxy-, iso-propoxy- ortrifluoromethyl-substituted C₃-C₄-alkanediyl in which optionally two notdirectly adjacent members are replaced by oxygen.

Het very particularly preferably represents one of the groups

G very particularly preferably represents hydrogen (a) or veryparticularly preferably represents one of the groups

(in particular represents (a), (b) or (c))

in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ very particularly preferably represents in each case optionallychlorine- or fluorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₁-C₆-alkyl, C₁-C₄-alkylthio-C₁-C₆-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or very particularly preferably representsoptionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-,n-butyl-, i-butyl-, tert-butyl-, methoxy-, ethoxy-, n-propoxy- oriso-propoxy-substituted C₃-C₆-cycloalkyl, in which optionally one or twonot directly adjacent methylene groups are replaced by oxygen and/orsulphur,

very particularly preferably represents optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-,methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-,ethylthio-, methylsulphonyl- or ethylsulphonyl-substituted phenyl,

very particularly preferably represents optionally fluorine-, chlorine-,bromine-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,trifluoromethyl- or trifluoromethoxy-substituted benzyl,

very particularly preferably represents in each case optionallyfluorine-, chlorine-, bromine-, methyl- or ethyl-substituted furanyl,thienyl or pyridyl, very particularly preferably represents optionallyfluorine-, chlorine-, methyl- or ethyl-substituted phenoxy-C₁-C₄-alkylor

very particularly preferably represents in each case optionallyfluorine-, chlorine-, amino-, methyl- or ethyl-substitutedpyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl orthiazolyloxy-C₁-C₄-alkyl.

R² very particularly preferably represents in each case optionallyfluorine- or chlorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₂-C₆-alkyl or poly-C₁-C₄-alkoxy-C₂-C₆-alkyl,

very particularly preferably represents optionally fluorine-, chlorine-,methyl-, ethyl-, n-propyl, iso-propyl- or methoxy-substitutedC₃-C₆-cycloalkyl,

or very particularly preferably represents in each case optionallyfluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-,i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl or benzyl.

R³ very particularly preferably represents in each case optionallyfluorine- or chlorine-substituted methyl, ethyl, propyl, iso-propyl,n-butyl, tert-butyl, or very particularly preferably represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-,iso-propyl-, tert-butyl-, methoxy-, ethoxy-, iso-propoxy-,trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenylor benzyl.

R⁴ and R⁵ independently of one another each very particularly preferablyrepresent in each case optionally fluorine- or chlorine-substitutedC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino orC₁-C₄-alkylthio or very particularly preferably represent in each caseoptionally fluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-,methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl,phenoxy or phenylthio.

R⁶ and R⁷ independently of one another very particularly preferablyrepresent hydrogen, very particularly preferably represent in each caseoptionally fluorine- or chlorine-substituted C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl orC₁-C₄-alkoxy-C₂-C₄-alkyl, very particularly preferably represent in eachcase optionally fluorine-, chlorine-, bromine-, methyl-, methoxy- ortrifluoromethyl-substituted phenyl or benzyl, or together veryparticularly preferably represent an optionally methyl- orethyl-substituted C₅-C₆-alkylene radical in which optionally onemethylene group is replaced by oxygen or sulphur.

The abovementioned general or preferred definitions of radicals orillustrations can be combined with each other as desired, that is to saycombinations between the ranges and preferred ranges in question arealso possible. They apply both to the end products and, correspondingly,to the starting materials and intermediates.

Preference according to the invention is given to those compounds of theformula (I) which contain a combination of the definitions given aboveas being preferred (preferable).

Particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of thedefinitions given above as being particularly preferred.

Very particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of thedefinitions given above as being very particularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,may be, also in combination with heteroatoms such as, for example, inalkoxy, in each case straight-chain or branched as far as is possible.

Optionally substituted radicals may be mono- or polysubstituted, itbeing possible for the substituents in the case of polysubstitutions tobe identical or different.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be mentionedspecifically:

TABLE 1 (l-1-a)

V X W Y Z H Br H Cl H H Cl H Br H H Cl H Cl H H Cl H F H H F H Cl H H ClH OCH₃ H H Cl H CH₃ H H OCH₃ H Cl H H OCH₃ H OCH₃ H H CH₃ H Cl H H CH₃ HF H H CH₃ H OCH₃ H H CH₃ H t-C₄H₉ H H CH₃ H CH₃ H H Cl Cl H H H Cl F H HH Cl OCH₃ H H H Cl CH₃ H H H Cl OC₂H₅ H H H OCH₃ OCH₃ H H H CH₃ CH₃ H HH Br CH₃ Br H H Cl Cl CH₃ H H CH₃ Br CH₃ H H CH₃ Cl CH₃ H H CH₃ OCHF₂CH₃ H H CH₃ OCH₂CF₃ CH₃ H H CH₃ OC₂H₅ CH₃ H H CH₃ OCH₃ CH₃ H H CH₃ CH₃CH₃ H H Br Br CH₃ H H Cl Cl CH₃ H H C₂H₅ C₂H₅ Br H H CH₃ CH₃ Br H H CH₃CH₃ OCH₃ H H Br Cl CH₃ H H Br CH₃ Cl H H Cl CH₃ Br H H C₂H₅ Br CH₃ H HCH₃ O—C₃H₇ CH₃ H H CH₃ O—Bz* CH₃ H H CH₃ CH₃ Cl H H CH₃ Ph* CH₃ H H Cl HCl Cl H CH₃ H CH₃ CH₃ H CH₃ H Cl CH₃ H Br H Cl CH₃ H Br H CH₃ CH₃ H Cl HBr CH₃ H Cl H Cl CH₃ H CH₃ H Br CH₃ H Cl H Cl F H Cl H —O—CF₂—O— H Br H—(CH₂)₃— H Cl H CH₃ Cl H CH₃ H H H H Cl H H H H Br H H H H O—Bz H H H HCF₃ H H H H OCH₃ H H H H CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ H CH₃ CH₃ CH₃ CH₃ CH₃ HCH₃ H Br Br —(CH₂)₃— H CH₃ CH₃ CH₃ F H CH₃ CH₃ CH₃ Cl H CH₃ CH₃ CH₃ Br HCH₃ CH₃ H Cl H CH₃ CH₃ H Br H Cl Cl H Br CH₃ CH₃ CH₃ CH₃ CH₃ *Bz =benzyl; Ph = phenyl

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-2-a) may be mentionedspecifically.

in which

V, W, X, Y and Z are each as defined in Table 1.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-3-a) may be mentionedspecifically.

in which

V, W, X, Y and Z are each as defined in Table 1.

Using according to process (A)N-[(4-chloro-2,6-dimethyl)-phenylacetyl]-3-amino-3-carboxyethyl-tetrahydropyranas starting material, the course of the process according to theinvention can be represented by the following equation:

Using according to process (B)O-[(2-chloro-6-methyl)-phenylacetyl]-3-hydroxy-3-carboxyethyl-tetrahydropyranas starting material, the course of the process according to theinvention can be represented by the following equation:

Using according to process (c) ethyl2-[(2-chloro-4,6-dimethyl)-phenyl]-4-(4-methoxy)-benzylmercapto-4,4-methyleneoxypropyl-3-oxo-valerate,the course of the process according to the invention can be representedby the following equation:

Using according to process (Dα)3-[(2-chloro-4-methyl)-phenyl]-5,5-methyleneoxypropyl-pyrrolidine-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

Using according to process (D) (Variant β)3-[(2,4-dichloro)-phenyl]-4-hydroxy-5,5-methyleneoxypropyl-Δ³-dihydrofuran-2-oneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

Using according to process (E)8-[(2,4-dichloro)-phenyl]-5,5-methyleneoxypropyl-pyrrolidine-2,4-dioneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

Using according to process (F)3-[(2,6-dibromo-4-methyl)-phenyl]-4-hydroxy-5,5-methyleneoxypropyl-Δ³-dihydrofuran-2-oneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

Using according to process (G)2-[(2,4,6-trimethyl)-phenyl]-5,5-methyleneoxypropyl-pyrrolidine-2,4-dioneand methanesulphonyl chloride as starting material, the course of thereaction can be represented by the following equation:

Using according to process (H)2-[(4-bromo-2-chloro-6-methyl)-phenyl]-4-hydroxy-5,5-methyleneoxypropyl-Δ³-dihydrofuran-2-oneand (2,2,2-trifluoroethyl) methanethio-phosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing equation:

Using according to process (I)3-[(2,4-dichloro)-6-methylphenyl]-5,5-methyleneoxypropyl-pyrrolidine-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the following equation:

Using according to process (J) (variant α)3-[(2-chloro-4-bromo-5-methyl)-phenyl]-4-hydroxy-5,5-methyleneoxypropyl-Δ³-dihydrofuran-2-oneand ethylisocyanate as starting materials, the course of the reactioncan be represented by the following equation:

Using according to process (J) (variant β)3-[(2-chloro-4,6-dimethyl)-phenyl]-5,5-methyleneoxypropyl-pyrrolidine-2,4-dioneand dimethylcarbamidoyl chloride as starting materials, the course ofthe reaction can be represented by the following equation:

The compounds of the formula (II) required as starting materials in theprocess (A) according to the invention

in which

V, W, X, Y, Z and R⁸ are each as defined above

are novel.

The acylamino acid esters of the formula (II) are obtained, for example,when amino acid derivatives of the formula (XV)

in which

R⁸ is as defined above

are acylated with substituted phenylacetyl halides of the formula (XVI)

in which

V, W, X, Y and Z are each as defined above and

Hal represents chlorine or bromine

(Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6,341-5, 1968),

or when acylamino acids of the formula (XVII)

in which

V, W, X, Y and Z are each as defined above

are esterified (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XVII)

in which

V, W, X, Y and Z are each as defined above

are novel.

Compounds of the formula (XVII) are obtained, for example, when3-amino-tetrahydropyran-3-carboxylic acid of the formula (XVIII)

is acylated according to Schotten-Baumann (Organikum, VEB DeutscherVerlag der Wissenschaften, Berlin 1977, p. 505) with substitutedphenylacetyl halides of the formula (XVI)

in which

V, W, X, Y and Z are each as defined above and

Hal represents chlorine or bromine.

Some of the compounds of the formula (XVI) are novel and can be preparedby known processes (cf., for example, WO 97/02 243, WO 97/01 535 andDE-196 13 171).

The compounds of the formula (XVI) are obtained, for example, byreacting substituted phenylacetic acids of the formula (XIX)

in which

V, W, X, Y and Z are each as defined above

with halogenating agents (for example thionyl chloride, thionyl bromide,oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromideor phosphorus pentachloride), if appropriate in the presence of adiluent (for example optionally chlorinated aliphatic or aromatichydrocarbons such as toluene or methylene chloride) at temperatures offrom −20° C. to 150° C., preferably of from −10° C. to 100° C.

Some of the compounds of the formula (XIX) are novel, they can beprepared by processes known from the literature (Organikum 15th edition,p. 533, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, cf., forexample, WO 97/02 243, WO 07/01 535 and DE-196 13 171). The compounds ofthe formula (XIX) are obtained, for example, by hydrolyzing substitutedphenylacetic acids of the formula (XX)

in which

V, W, X, Y, Z and R⁸ are each as defined above

in the presence of an acid (for example an inorganic acid such ashydrochloric acid) or a base (for example an alkali metal hydroxide suchas sodium hydroxide or potassium hydroxide) and, if appropriate, adiluent (for example an aqueous alcohol such as methanol or ethanol) attemperatures between 0° C. and 150° C., preferably between 20° C. and100° C.

Some of the compounds of the formula (XX) are novel, they can beprepared by processes known in principle.

The compounds of the formula (XX) are obtained, for example, by reactingsubstituted 1,1,1-trichloro-2-phenylethanes of the formula (XXI)

in which

V, W, X, Y and Z are each as defined above initially with alkoxides (forexample alkali metal alkoxides such as sodium methoxide or sodiumethoxide) in the presence of a diluent (for example of the alcoholderived from the alkoxide) at temperatures between 0° C. and 150° C.,preferably between 20° C. and 120° C. and subsequently reacting with anacid (preferably an inorganic acid, such as, for example, sulphuricacid) at temperatures between −20° C. and 150° C., preferably between 0°C. and 100° C., (cf. DE-3 314 249).

Some of the compounds of the formula (XXI) are novel, they can beprepared by processes known in principle.

The compounds of the formula (XXI) are obtained, for example, whenanilines of the formula (XXII)

in which

V, W, X, Y and Z are each as defined above

are reacted in the presence of an alkyl nitrite of the formula (XXIII)

R¹³-ONO  (XXIII)

in which

R¹³ represents alkyl, preferably C₁-C₆-alkyl,

in the presence of copper (II) chloride and if appropriate in thepresence of a diluent (for example an aliphatic nitrile such asacetonitrile) at a temperature of from −20° C. to 80° C., preferablyfrom 0° C. to 60° C., with vinylidene chloride (CH₂═CCl₂).

Some of the compounds of the formula (XXII) are known. However, they canbe prepared by processes known from the literature, for example byreducing the corresponding nitro compounds or by halogenating theanilines or acetanilines, followed by recleavage.

The compounds of the formula (XXIII) are known compounds of organicchemistry. Copper(II) chloride and vinylidene chloride have been knownfor a long time and are commercially available.

The compounds of the formula (XV) and (XVIII) are novel. They can beprepared by known processes (see, for example Compagnon, Ann. Chim.(Paris) [14] 5, p. 11-22, 23-27 (1970), L. Munday, J. Chem. Soc. 4372(1961); J. T. Edward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975).

Furthermore, the starting materials of the formula (II)

in which

V, W, X, Y, Z and R⁸ are each as defined above

used in the process (A) can be prepared when3-amino-tetrahydropyran-3-carbonitrile of the formula (XXIV)

is reacted with substituted phenylacetyl halides of the formula (XVI)

in which

V, W, X, Y, Z and Hal are each as defined above

to give compounds of the formula (XXV)

in which

V, W, X, Y and Z are each as defined above

and these are subsequently subjected to acid alcoholysis.

The compounds of the formula (XXV) are also novel. The compounds of theformula (XXIV) are also novel (see Preparation Example).

The compounds of the formula (III)

in which

V, W, X, Y, Z and R⁸ are each as defined above

required as starting materials in the process (B) according to theinvention are novel.

They can be prepared in a simple manner by methods known in principle.

The compounds of the formula (III) are obtained, for example, when

3-hydroxy-tetrahydropyran-3-carboxylic esters of the formula (XXVI)

in which

R⁸ is as defined above

are acylated with substituted phenylacetyl halides of the formula (XVI)

in which

V, W, X, Y, Z and Hal are each as defined above

(Chem. Reviews 52, 237-416 (1953)).

The 3-hydroxy-tetrahydropyran-3-carboxylic esters of the formula (XXVI)are novel. They are obtained, for example, by alcoholizing3-hydroxy-tetrahydropyran-3-carbonitrile of the formula (XXVI-a) in thepresence of acids, for example according to Pinner (see PreparationExample). The cyanohydrin is obtained, for example, by reactingtetrahydropyran-3-one with hydrocyanic acid.

The compounds of the formula (IV)

in which

T, V, W, X, Y, Z and R⁸ are each as defined above

required as starting materials in the above process (C) are novel.

They can be prepared by methods known in principle.

The compounds of the formula (IV) are obtained, for example, whensubstituted phenylacetic esters of the formula (XX)

in which

V, W, X, Y, R⁸ and Z are each as defined above

are acylated with 2-benzylthio-carbonyl halides of the formula (XXVII)

in which

T is as defined above and

Hal represents halogen (in particular chlorine or bromine) in thepresence of strong bases (see, for example, M. S. Chambers, E. J.Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun., (1987), 1228).

The benzylthio-carbonyl halides of the formula (XXVII) are novel. Theycan be prepared by known processes (J. Antibiotics (1983), 26, 1589).

The acyl halides of the formula (V), carboxylic anhydrides of theformula (VI), chloroformic esters or chloroformic thioesters of theformula (VII), chloromonothioformic esters or chlorodithioformic estersof the formula (VIII), sulphonyl chlorides of the formula (IX),phosphorus compounds of the formula (X) and metal hydroxides, metalalkoxides or amines of the formula (XI) and (XII) and isocyanates of theformula (XIII) and carbamoyl chlorides of the formula (XIV) furthermorerequired as starting materials for carrying out the processes (D), (E),(F), (G), (H), (I) and (J) according to the invention are generallyknown compounds of organic or inorganic chemistry.

The compounds of the formulae (XVI), (XIX), (XX), (XXI) and (XXII) arefurthermore known from the patent applications cited at the outsetand/or can be prepared by methods given therein (cf. also WO 96/35 664,WO 97/01 535, WO 97/02 243 and DE-196 13 171).

The process (A) is characterized in that compounds of the formula (II)in which V, W, X, Y, Z and R⁸ are each as defined above are subjected toan intramolecular condensation in the presence of a diluent and in thepresence of a base.

Suitable diluents for use in the process (A) according to the inventionare all organic solvents which are inert towards the reactants.Preference is given to using hydrocarbons, such as toluene and xylene,furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone, and also alcohols such as methanol, ethanol,propanol, iso-propanol, butanol, iso-butanol and tert-butanol.

Suitable bases (deprotonating agents) for use in the practice of theprocess (A) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which may also be used in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). It is also possible to use alkalimetals such as sodium or potassium. Furthermore, it is possible to usealkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and moreover alsoalkali metal alkoxides, such as sodium methoxide, sodium ethoxide andpotassium tert-butoxide.

When carrying out the process (A) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −75° C. and200° C., preferably between −50° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction component of the formula (II) and the deprotonating base aregenerally employed in equimolar to about doubly-equimolar amounts.However, it is also possible to use one component or the other in arelatively large excess (upto 3 mol).

The process (B) is characterized in that compounds of the formula (m) inwhich V, W, X, Y, Z and R⁸ are each as defined above areintramolecularly condensed in the presence of a diluent and in thepresence of a base.

Suitable diluents for use in the process (B) according to the inventionare all solvents which are inert towards the reactants. Preference isgiven to using hydrocarbons, such as toluene and xylene, furthermoreethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethylether and diglycol dimethyl ether, moreover polar solvents, such asdimethyl sulphoxide, sulpholane, dimethylformamide andN-methylpyrrolidone. Furthermore, it is possible to use alcohols such asmethanol, ethanol, propanol, iso-propanol, butanol, iso-butanol andtert-butanol.

Suitable bases (deprotonating agents) for use in the practice of theprocess (B) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which may also be used in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). It is also possible to use alkalimetals such as sodium or potassium. Furthermore, it is possible to usealkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and moreover alsoalkali metal alkoxides, such as sodium methoxide, sodium ethoxide andpotassium tert-butoxide.

When carrying out the process (B) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −75° C. and200° C., preferably between −50° C. and 150° C.

The process (B) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (B) according to the invention, thereaction components of the formula (III) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use one component or the other in a relatively largeexcess (upto 3 mol).

Process (C) is characterized in that compounds of the formula (IV) inwhich T, V, W, X, Y, Z and R⁸ are each as defined above areintramolecularly cyclized in the presence of an acid and, ifappropriate, in the presence of a diluent.

Suitable diluents for use in the process (C) according to the inventionare all organic solvents which are inert towards the reactants.Preference is given to using hydrocarbons, such as toluene and xylene,furthermore halogenated hydrocarbons, such as dichloromethane,chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, moreoverpolar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone. Furthermore, it is alsopossible to use alcohols such as, methanol, ethanol, propanol,iso-propanol, butanol, iso-butanol, tert-butanol.

If appropriate, the acid used can also serve as diluent.

Suitable acids for use in the process (C) according to the invention areall customary inorganic and organic acids, such as, for example,hydrohalic acids, sulphuric acid, alkyl-, aryl-, and haloalkylsulphonicacids, and use is made in particular of halogenated alkylcarboxylicacids, such as, for example, trifluoroacetic acid.

When carrying out the process (C) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thereaction components of the formula (IV) and the acid are employed, forexample, in equimolar amounts. However, it is also possible, ifappropriate, to use catalytic amounts of the acid.

The process (Dα) is characterized in that compounds of the formulae(I-1-a) to (I-3-a) are in each case reacted with carbonyl halides of theformula (V), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Suitable diluents for use in the process (Dα) according to the inventionare all solvents which are inert towards the acyl halides. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetraline, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such asdimethylfonnamide, dimethyl sulphoxide and sulpholane. The hydrolyticstability of the acyl halide permitting, the reaction can also becarried out in the presence of water.

Suitable acid binders for the reaction according to process (Dα)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hunig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, and also alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate and also alkalie metal hydroxides such as sodium hydroxide andpotassium hydroxide.

The reaction temperature of the process (Dα) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures between −20° C. and +150° C., preferablybetween 0° C. and 100° C.

When carrying out the process (Dα) according to the invention, thestarting materials of the formulae (I-1-a) to (I-3-a) and the carbonylhalide of the formula (V) are generally each employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (upto 5 mol) of the carbonyl halide.

Work-up is carried out by customary methods.

The process (Dβ) is characterized in that compounds of the formulae(I-1-a) to (I-3-a) are each reacted with carboxylic anhydrides of theformula (VI), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Suitable diluents for use in the process (Dβ) according to the inventionare preferably those diluents which are also preferred when acyl halidesare used. Additionally, a carboxylic anhydride employed in excess canalso simultaneously act as diluent.

The acid binders which are, if appropriated added in the process (Dβ)are preferably those acid binders which are also preferred when acylhalides are used.

The reaction temperature in the process (Dβ) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures beween −20° C. and +150° C., preferablybetween 0° C. and 100° C.

When carrying out the process (Dβ) according to the invention, thestarting materials of the formulae (I-1-a) to (I-3-a) and the carboxylicanhydride of the formula (VI) are generally each employed inapproximately equivalent amounts. However, it is also possible to employa relatively large excess (upto 5 mol) of carboxylic anhydride. Work-upis carried out by customary methods.

In general, diluent and excess carboxylic anhydride and also thecarboxylic acid formed are removed by distillation or by washing with anorganic solvent or with water.

The process (E) is characterized in that compounds of the formulae(I-1-a) to (I-3-a) are in each case reacted with chloroformic esters orchloroformic thiol esters of the formula (VII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

Acid binders which are suitable for the process (E) according to theinvention are all customary acid acceptors. Preference is given to usingtertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN,Huinig base and N,N-dimethyl-aniline, furthermore alkaline earth metaloxides, such as magnesium oxide and calcium oxide, moreover alkali metaland alkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal hydroxides suchas sodium hydroxide and potassium hydroxide.

Suitable diluents for use in the process (E) according to the inventionare all solvents which are inert towards the chloroformic esters orchloroformic thio esters. Preference is given to using hydrocarbons,such as benzine, benzene, toluene, xylene and tetralin, furthermore,halogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl ispropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, moreover nitrites such as acetonitrileand also strongly polar solvents, such as dimethylformamide, dimethylsulphoxide and sulpholane.

When carrying out the process (E) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction temperature is between −20° C. and +100° C.,preferably between 0° C. and 50° C.

The process (E) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (E) according to the invention, thestarting materials of the formulae (I-1-a) to (I-3-a) and theappropriate chloroformic ester or chloroformic thiol ester of theformula (VII) are generally each employed in approximately equivalentamounts. However, it is also possible to employ one component or theother in a relatively large excess (up to 2 mol). Work-up is carried outby customary methods. In general, precipitated salts are removed and thereaction mixture which remains is concentrated by removing the diluentunder reduced pressure.

The process (F) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-3-a) are in each case reactedwith compounds of the formula (VIII) in the presence of a diluent and,if appropriate, in the presence of an acid binder.

In the preparation process (F), approximately 1 mol ofchloromonothioformic ester or chlorodithioformic ester of formula (VIII)per mole of starting material of the formulae (I-1-a) to (I-3-a) isreacted at 0 to 120° C., preferably at 20 to 60° C.

Diluents which may be added, if appropriate, are all inert polar organicsolvents, such as ethers, amides, sulphones, sulphoxides, and alsohalogenoalkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, ethyl acetate or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-3-a) is prepared by addition of strong deprotonating agents suchas, for example, sodium hydride or potassium tert-butoxide, the additionof acid binders can be dispensed with.

Suitable bases for use in the process (F) are all customary protonacceptors. Preference is given to using alkali metal hydrides, alkalimetal alkoxides, alkali metal or alkaline earth metal carbonates orbicarbonates or nitrogen bases. Examples include sodium hydride, sodiummethoxide, sodium hydroxide, calcium hydroxide, potassium carbonate,sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine,pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene(DBN) and diazabicycloundecene (DBU).

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (G) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-3-a) are in each case reactedwith sulphonyl chlorides of the formula (IX), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (G), approximately 1 mol of sulphonylchloride of the formula (IX) per mole of starting material of theformula (I-1-a) to (I-3-a) is reacted at −20 to 150° C., preferably at 0to 70° C.

The process (G) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert polar organic solvents such as ethers,amides, ketones, carboxylic esters, nitrites, sulphones, sulphoxides orhalogenated hydrocarbons such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, ethyl acetate, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-3-a) is prepared by addition of strong deprotonating agents (suchas, for example, sodium hydride or potassium tert-butoxide), theaddition of acid binders can be dispensed with.

If acid binders are used, then customary inorganic or organic bases aresuitable, examples being sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (H) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-3-a) are in each case reactedwith phosphorus compounds of the formula (X), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (H), 1 to 2, preferably 1 to 1.3, mol of thephosphorus compound of the formula (X) are reacted per mole of thecompounds (I-1-a) to (I-3-a), at temperatures between −40° C. and 150°C., preferably between −10 and 110° C., to obtain compounds of theformulae (I-1-e) to (I-3-e).

The process (H) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert, polar organic solvents such as ethers,carboxylic esters, halogenated hydrocarbons, ketones, amides, nitrites,sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

Acid binders which are added, if appropriate, are customary inorganic ororganic bases, such as hydroxides, carbonates or amines. Examplesinclude sodium hydroxide, sodium carbonate, potassium carbonate,pyridine and triethylamine.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out according to customary methods oforganic chemistry. The end products are preferably purified bycrystallization, chromatographic purification or by so-called “encipientdistillation”, i.e. removal of the volatile components under reducedpressure.

The process (I) is characterized in that compounds of the formulae(I-1-a) to (I-3-a) are in each case reacted with metal hydroxides ormetal alkoxides of the formula (XI) or amines of the formula (XII), ifappropriate in the presence of a diluent.

Diluents which are preferred for use in the process (I) according to theinvention are ethers such as tetrahydrofuran, dioxane, diethyl ether, orelse alcohols such as methanol, ethanol, isopropanol, but also water.The process (I) according to the invention is generally carried outunder atmospheric pressure. The reaction temperature is generallybetween −20° C. and 100° C., preferably between 0° C. and 50° C.

The process (J) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-3-a) are in each case reactedwith (Jα) compounds of the formula (XIII), if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or (Jβ) with compounds of the formula (XIV), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (Jα), approximately 1 mol of isocyanate ofthe formula (XI) is reacted per mole of starting material of theformulae (I-1-a) to (I-3-a) at 0 to 100° C., preferably at 20 to 50° C.

The process (Jα) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert organic solvents, such as aromatichydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles,sulphones or sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Catalysts which can be employed very advantageously are organotincompounds, such as, for example, dibutyltin dilaurate.

The process is preferably carried out under atmospheric pressure.

In the preparation process (Jβ), approximately 1 mol of carbamoylchloride of the formula (XIV) is reacted per mole of starting materialof the formulae (I-1-a) to (I-3-a) at 0 to 150° C., preferably at 20 to70° C.

Diluents which may be added, if appropriate, are all inert polar organicsolvents such as ethers, carboxylic esters, nitrites, ketones, amides,sulphones, sulphoxides or halogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-1-a)to (I-3-a) is prepared by addition of strong deprotonating agents (suchas, for example, sodium hydride or potassium tert-butoxide), theaddition of acid binders can be dispensed with.

If acid binders are employed, then customary inorganic or organic basesare suitable, examples including sodium hydroxide, sodium carbonate,potassium carbonate, triethylamine or pyridine.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The active compounds are suitable for controlling animal pests,preferably arthropods and nematodes, in particular insects andarachnida, which are encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienefield. They are active against normally sensitive and resistant speciesand against all or some stages of development. The abovementioned pestsinclude:

From the order of Isopoda, for example, Oniscus asellus, Armadillidiumvulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blatella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dernaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Frankliniellaoccidentalis, Hercinothrips femoralis, Thrips palmi and Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi. Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium comi, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp, Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelidesobtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsadecemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodeschrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilussurinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus,Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica,Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctusspp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbiumpsylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derusspp., Melolontha melolontha, Amphimallon soisti tialis and Costelytrazealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Liriomyza spp., Stomoxys spp.,Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibiohortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitiscapitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The active compounds according to the invention have a high insecticidaland acaricidal activity.

They can be used to particularly good effect for controlling insectswhich are injurious to plants, such as, for example, against the larvaeof the mustard beetle (Phaedon cochleariae), or against the larvae ofthe green rice leaf hopper (Nephotettix cincticeps) and against thecaterpillars of the cabbage moth (Plutella maculipennis).

The active compounds according to the invention can furthermore be usedas defoliants, desiccants, haulm killers and, especially, asweedkillers. By weeds, in the broadest sense, there are to be understoodall plants which grow in locations where they are not wanted. Whetherthe substances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The doses of the active compounds according to the invention necessaryto control weeds are between 0.001 and 10 kg/ha, preferably between0.005 and 5 kg/ha.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotola, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railtracks, and on paths and squares with and without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial crops, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land and for the selective control of weeds inannual crops.

The active compounds according to the invention are particularlysuitable for the selective control of monocotyledonous weeds indicotyledonous crops, both pre-emergence and post-emergence. In cottonand sugar beet, for example, they can be employed very successfully forcontrolling weed grasses.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifying agents and/or dispersing agents and/or foam-forming agents.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Essentially, suitable liquidsolvents include: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes of methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and also water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montrnorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates, suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;suitable emulsifying and/or foam-forming agents are: for examplenon-ionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates andalso protein hydrolysates; suitable dispersing agents are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%, andadditionally preferably extenders and surfactants.

The active compound according to the invention can be present in itscommercially available fonnulations and in the use forms prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphates, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas and substances produced by microorganisms.

Examples of particularly advantageous mixture components are thefollowing compounds:

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2′,6′-dibromo-2-methyl-4′-trifluoromethoxy4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methox-imino-[alpha-(o-tolyloxy)-o-tolyl]-acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulphamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, irnibenconazole, iminoctadine, iprobenfos (IBP), iprodione,isoprothiolane, kasugamycin, copper preparations such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole, methasulphocarb, methfuroxam, metiram, metsulphovax,myclobutanil,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin,piperalin, polycarbamate, polyoxin, probenazole, prochloraz,procymidone, propamocarb, propiconazole, propineb, pyrazophos,pyrifenox, pyrimethanil, pyroquilon,

quintozene (PCNB),

sulphur and sulphur preparations,

tebucanozole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumizole, triforine, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,beta-cyluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxin, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphane, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulphoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,

ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivemectin, lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mevinphos, mesulphenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirirnicarb, pirimiphos M, primiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulphotep, sulprofos,

tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides:

for example anilides such as, for example, diflufenican and propanil;arylcarboxylic acids such as, for example, dichloropicolinic acid,dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4-D,2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones such as, for example, chloridazon andnorflurazon; carbamates such as, for example, chlorpropham, desmedipham,phenmedipham and propham; chloroacetanilides such as, for example,alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlorand propachlor; dinitroanilines such as, for example, oryzalin,pendimethalin and trifluralin; diphenyl ethers such as, for example,acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen andoxyfluorfen; ureas such as, for example, chlortoluron, diuron,fluometuron, isoproturon, linuron and methabenz-thiazuron;hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim,sethoxydim and tralkoxydim; imidazolinones such as, for example,imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as,for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as,for example, mefenacet; sulphonylureas such as, for example,amidosulphuron, bensulphuron-methyl, chlorimuron-ethyl, chlorsulphuron,cinosulphuron, metsulphuron-methyl, nicosulphuron, primisulphuron,pyrazosulphuron-ethyl, thifensulphuron-methyl, triasulphuron andtribenuron-methyl; thiocarbamates such as, for example, butylate,cycloate, di-allate, EPTC, esprocarb, molinate, prosulphocarb,thiobencarb and tri-allate; triazines such as, for example, atrazine,cyanazine, simazine, simetryne, terbutryne and terbutylazine;triazinones such as, for example, hexazinone, metamitron and metribuzin;others such as, for example, aminotriazole, benfuresate, bentazone,cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr,ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben,pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

The active compound according to the invention can furthermore bepresent in its commercially available formulations and in the use formsprepared from these formulations, as a mixture with synergistic agents.Synergistic agents are compounds which increase the action of the activecompounds without it being necessary for the synergistic agent added tobe active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound has excellent residual action on wood and clay and also a goodstability to alkali on limed substrates.

The active compounds according to the invention are not only activeagainst plant, hygiene and stored-product pests, but also, in theveterinary medicine sector, against animal parasites (ectoparasites),such as ixodid ticks, argasid ticks, scab mites, trombiculid mites,flies (stinging and sucking), parasitic fly larvae, lice, hair lice,bird lice and fleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the sub-orders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

From the order Diptera and the sub-orders Nematocerina and Brachycerina,for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp.,Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the sub-class of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example Argas spp., Ornithodorus spp., Otabiusspp., Ixodes spp., Amblyommna spp., Boophilus spp., Dermacentor spp.,Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Octodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which attack agriculturallivestock, such as, for example, cattle, sheep, goats, horses, pigs,donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese,honey bees, other domestic animals, such as, for example, dogs, cats,cage birds, aquarium fish, and so-called experimental animals such as,for example, hamsters, guinea-pigs, rats and mice. By controlling thesearthropods, it is intended to reduce mortality and decreased performance(in meat, milk, wool, hides, eggs, honey and the like), so that moreeconomical and simpler animal keeping is made possible by using theactive compounds according to the invention.

In the veterinary sector, the active compounds according to theinvention are used in a known manner by enteral administration, forexample in the form of tablets, capsules, drinks, drenches, granules,pastes, boluscs, the feed-through method, suppositories, by parenteraladministration, such as, for example, by means of injections(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal application, by dermal administration, forexample in the form of dipping or bathing, spraying, pouring-on andspotting-on, washing, dusting, and with the aid of shaped articles whichcomprise active compound, such as collars, ear tags, tail marks, limbbands, halters, marking devices and the like.

When administered to livestock, poultry, domestic animals and the like,the active compounds of the formula (I) can be used as formulations (forexample powders, emulsions, flowables) which comprise the activecompounds in an amount of 1 to 80% by weight, either directly or afterdilution by a factor of 100 to 10,000, or they may be used in the formof a chemical bath.

Furthermore, it has been found that the compounds of the formula (I)according to the invention have a potent insecticidal action againstinsects which destroy industrial materials.

The following insects may be mentioned by way of example and as beingpreferred, but without any limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

Dermapterans, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus.

Bristletails, such as

Lepisma saccharina.

Industrial materials are to be understood as meaning, in the presentcontext, non-live materials such as, preferably, synthetic materials,glues, sizes, paper and board, leather, wood and timber products, andpaint.

The materials to be very particularly preferably protected againstattack by insects are wood and timber products.

Wood and timber products which can be protected by the compositionaccording to the invention or mixtures comprising such a composition areto be understood as meaning, for example: construction timber, woodenbeams, railway sleepers, bridge components, jetties, wooden vehicles,boxes, pallets, containers, telephone poles, wood lagging, windows anddoors made of wood, plywood, particle board, joiner's articles, or woodproducts which, quite generally, are used in the construction of housesor in joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations, such as powders, granules, solutions,suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if appropriate desiccants and UV stabilizers and, ifappropriate, colorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for the protection ofwood and wooden materials comprise the active compound according to theinvention at a concentration of 0.0001 to 95% by weight, in particular0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thespecies and the occurrence of the insects and on the medium. The optimumrate of application can be determined upon use in each case by testseries. However, in general, it suffices to employ 0.0001 to 20% byweight, preferably 0.001 to 10% by weight, of the active compound, basedon the material to be protected.

The solvent and/or diluent used is an organochemnical solvent or solventmixture and/or an oily or oil-type organochemical solvent or solventmixture of low volatility and/or a polar organochemical solvent orsolvent mixture and/or water and, if appropriate, an emulsifier and/orwetting agent.

Organochemical solvents which are preferably employed are oily oroil-type solvents having an evaporation number of above 35 and aflashpoint of above 30° C., preferably above 45° C. Substances which areused as such oily and oil-type solvents which have low volatility andare insoluble in water are suitable mineral oils or their aromaticfractions, or mineral-oilcontaining solvent mixtures, preferably whitespirit, petroleum and/or alkylbenzene.

Substances which are advantageously used are mineral oils with a boilingrange of 170 to 220° C., white spirit with a boiling range of 170 to220° C., spindle oil with a boiling range of 250 to 350° C., petroleumor aromatics of boiling range 160 to 280° C., essence of turpentine andthe like.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boilingrange of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility having anevaporation number of above 35 and a flashpoint of above 30° C.,preferably above 45° C., can be partially replaced by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flashpoint ofabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

In a preferred embodiment, part of the organochemical solvent or solventmixture is replaced by an aliphatic polar organochemical solvent orsolvent mixture. Substances which are preferably used are aliphaticorganochemical solvents having hydroxyl and/or ester and/or ethergroups, such as, for example, glycol ether, esters and the like.

The organochemical binders used within the scope of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se and can be diluted with water and/or are soluble ordispersible or emulsifiable in the organochemical solvents employed, inparticular binders composed of, or comprising, an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenol resin, hydrocarbon resin, such asindene/coumarone resin, silicone resin, drying vegetable and/or dryingoils and/or physically drying binders based on a natural and/orsynthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Up to 10% by weight of bitumen orbituminous substances can also be used as binders. In addition,colorants, pigments, water repellents, odour-masking substances andinhibitors or anticorrosives known per se and the like can also beemployed.

The composition or the concentrate preferably comprises, in accordancewith the invention, at least one alkyd resin or modified alkyd resinand/or a drying vegetable oil as the organochemical binder. Preferablyused according to the invention are alkyd resins with an oil content ofover 45% by weight, preferably 50 to 68% by weight.

All or some of the abovementioned binder can be replaced by a fixative(mixture) or a plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate,the phosphoric esters, such as tributyl phosphate, the adipic esters,such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearateor amyl stearate, the oleates, such as butyl oleate, the glycerol ethersor relatively high-molecular-weight glycol ethers, glycerol esters andp-toluene-sulphonic esters.

Fixatives are chemically based on polyvinyl alkyl ethers, such as, forexample, polyvinyl methyl ether, or ketones, such as benzophenone orethylene benzophenone.

Particularly suitable as a solvent or diluent is also water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective protection of wood is achieved by large-scaleindustrial impregnation processes, for example vacuum, double-vacuum orpressure processes.

If appropriate, the ready-to-use compositions can additionally compriseother insecticides and, if appropriate, additionally one or morefungicides.

Suitable additional components which may be admixed are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in that document are expressly part of the presentapplication.

Very particularly preferred components which may be admixed areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorofluanide, tolylfluanide,3-iodo-2-propinylbutyl carbamate, N-octylsothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

The preparation and the use of the active compounds according to theinvention can be seen from the examples below.

EXAMPLES Example I-1-a-1

At reflux temperature, 17.3 g of the compound of Example II-1 in 160 mlof absolute toluene are added dropwise to 14.05 g (0.125 mol) ofpotassium tert-butoxide in 54 ml of absolute tetrahydrofuran (THF), andthe mixture is stirred at this temperature for another 1.5 hours. Aftercooling, 160 ml of water are added, the phases are separated, thetoluene phase is extracted with 80 ml of water and the combined aqueousphases are acidified with concentrated HCL at from 0 to 20° C. Theproduct is filtered off with suction, washed, dried and then, forfurther purification, stirred with methyl tert-butyl(MTB)ether/N-hexane,filtered off with suction and dried. Yield: 12.1 g (77% of theory),m.p.: 200° C.

Similarly, and/or according to the general preparation procedures, thefollowing compounds of the formula (I-1-a) are obtained:

TABLE 4 (I-1-a)

Ex. No. V W X Y Z m.p.° C I-1-a-2  H CH₃ CH₃ CH₃ CH₃ 219 I-1-a-3  H CH₃CH₃ Br H >220 I-1-a-4  H H CH₃ CH₃ H 226 I-1-a-5  H H Cl Cl H >220I-1-a-6  H H CH₃ CH₃ CH₃ 130 I-1-a-7  H H CH₃ H CH₃ 187 I-1-a-8  H Br ClCH₃ H >220 I-1-a-9  H H CH₃ Br CH₃ >220 I-1-a-10 H Cl CH₃ Cl H >220I-1-a-11 H H Br CH₃ CH₃ 145 I-1-a-12 H CH₃ CH₃ H Br 194 I-1-a-13 H CH₃CH₃ CH₃ Br

Example (I-1-b-1)

Under reflux, 2.88 g (0.010 mol) of the compound of Example (I-1-a-1)and 2.1 ml (15 nmol) of triethylamine in 50 ml of anhydrous ethylacetate are admixed with 1.85 ml (0.15 mol) of pivaloyl chloride in 5 mlof anhydrous ethyl acetate. The mixture is stirred under reflux untilthe reaction has, according to thin-layer-chromatographic analysis,ended. For work-up, the reaction mixture is concentrated, taken up inmethylene chloride, washed twice with 50 ml of 0.5 N aqueous sodiumhydroxide solution, dried over magnesium sulphate and concentrated. Thecrude product is recrystallized from MTB etherlN-hexane. Yield: 2.0 g(53% of theory), m.p.: 193° C.

Similarly, and/or according to the general preparation procedures, thefollowing compounds of the formula (I-b-1) are obtained:

TABLE 5 (I-1-b)

Ex. No. V W X Y Z R¹ m.p.° C. I-1-b-2  H CH₃ CH₃ CH₃ H i-C₃H₇ 163I-1-b-3  H CH₃ CH₃ CH₃ CH₃ i-C₃H₇ 153 I-1-b-4  H CH₃ CH₃ CH₃ CH₃2-thienyl >220 I-1-b-5  H CH₃ CH₃ Br H i-C₃H₇ 190 I-1-b-6  H CH₃ CH₃ BrH 2-thienyl >220 I-1-b-7  H CH₃ CH₃ Br H 4-Cl-phenyl 209 I-1-b-8  H CH₃H H CH₃ i-C₃H₇ 178 I-1-b-9  H CH₃ H CH₃ CH₃ i-C₃H₇ 173 I-1-b-10 H CH₃ HCH₃ CH₃ s-C₄H₉ 193 I-1-b-11 H CH₃ H CH₃ H i-C₃H₇ 183 I-1-b-12 H Cl H ClH i-C₃H₇ 108

Example (I-1-c-1)

At 0-10° C., 1.0 ml (0.010 mol) of ethyl chloroformate in 5 ml ofanhydrous methylene chloride are added dropwise to 2.88 g (0.010 mol) ofthe compound of Example (I-1-a-1) and 1.4 ml (0.010 mol) oftriethylamine in 50 ml of anhydrous CH₂Cl₂, and the mixture is stirredat room temperature until the reaction has, according tothin-layer-chromatographic analysis, ended. For work-up, the mixture iswashed twice with 50 ml of 0.5 N aqueous sodium hydroxide solution,dried over magnesium sulphate and concentrated. Yield: 2.8 g (77% oftheory), m.p.: 157° C.

Similarly, and/or according to the general preparation procedures, thefollowing compounds of the formula (I-1-c) are obtained:

TABLE 6 (I-1-c)

Ex. No. V W X Y Z L M R² m.p.° C. I-1-c-2 H CH₃ CH₃ CH₃ CH₃ O O C₂H₅ 163I-I-c-3 H CH₃ CH₃ Br H O O C₂H₅ 184 I-l-c-4 H H Cl Cl H O O C₂H₅ 131

Example II-1

At 30-40° C., 29.1 g (0.1016 mol) of the compound of Example (XXV-1) in310 ml of anhydrous methylene chloride are carefully added dropwise to51.3 g (0.513 mol) of conc. sulphuric acid, and the mixture is stirredat this temperature for 2 hours. 69 ml of absolute methanol are thenadded dropwise in such a way that an internal temperature ofapproximately 40° C. results, and stirring is continued at from 40 to70° C. for another 6 hours.

For work-up, the mixture is poured onto 0.51 kg of ice, extracted withmethylene chloride, washed with aqueous sodium bicarbonate solution,dried and concentrated. The residue is recrystallized from methyltert-butyl ether/N hexane. Yield: 17.3 g (53% of theory): m.p.: 168° C.

Similarly to Example (II-1) and according to the general preparationprocedures, the following compounds of the formula (II) are prepared.

TABLE 7 (II)

Ex. No. V W X Y Z R⁸ m.p.° C. II-2 H CH₃ CH₃ CH₃ CH₃ CH₃ 78 II-3 H CH₃CH₃ Br H CH₃ 110 II-4 H H CH₃ CH₃ H CH₃ 68 II-5 H H Cl Cl H CH₃ 103 II-6H H CH₃ CH₃ CH₃ CH₃ 92 II-7 H Br Cl CH₃ H CH₃ 114 II-8 H Cl CH₃ Cl H CH₃204 II-9 H H CH₃ H CH₃ CH₃ 74  II-10 H H CH₃ H H CH₃ 85  II-11 H H BrCH₃ CH₃ CH₃ 81  II-12 H H CH₃ Br CH₃ CH₃ 110  II-13 H CH₃ CH₃ H Br CH₃134  II-14 H H Cl —O—CF₂—O— CH₃ 121  II-15 H CH₃ CH₃ CH₃ Br CH₃ 97

Example XXV-1

At 0-10° C., 25 g of mesityleneacetyl chloride in 30 ml of absolute THFare added dropwise to 15.8 g of 3-aminotetrahydropyran-3-carbonitrile(according to Examnple XXIV) and 17.6 ml of triethylamine in 250 ml ofabsolute THF, and the mixture is stirred until the reaction has ended.The mixture is stirred into a mixture of 500 ml of ice-water and 200 mlof 1 N HCl. The product is filtered off with suction and the residue istaken up in methylene chloride, dried and concentrated. Yield: 29.1 g(81% of theory), m.p. 153° C.

Similarly to Example (XXV-1), and/or according to the generalpreparation procedures, the following compounds of the formula (XXV) areprepared:

TABLE 8 (XXV)

Ex. No. V W X Y Z m.p.° C. XXV-2 H CH₃ CH₃ CH₃ CH₃ 182 XXV-3 H CH₃ CH₃Br H 187 XXV-4 H H CH₃ CH₃ H 137 XXV-5 H H Cl Cl H 162 XXV-6 H H CH₃ CH₃CH₃ 159 XXV-7 H Br Cl CH₃ H 158 XXV-8 H Cl CH₃ Cl H 141 XXV-9 H H CH₃ HCH₃ 148  XXV-10 H H CH₃ H H 149  XXV-11 H CH₃ CH₃ H Br 176  XXV-12 H HBr CH₃ CH₃ 135  XXV-13 H H CH₃ Br CH₃ 166  XXV-14 H H Cl —O—CF₂O— 115 XXV-15 H CH₃ CH₃ CH₃ Br 212

Example I-2-a-1

At 10° C., 18.1 g (0.057 mol) of the compound of Example III-1 in 30 mlof dry dimethylformamide (DMF) are slowly added dropwise to 9.58 g(0.085 mol) of potassium tert-butoxide in 10 ml of dry DMF, and themixture is stirred at room temperature overnight. The DMF is distilledoff and the residue is taken up in 1 l of water and slowly acidifiedusing concentrated HCl. The product is filtered off with suction, washedwith water and dried under reduced pressure at 50° C. m.p. 261° C.

Similarly to Example (I-2-a-1) and according to the general procedures,the following compounds of the formula (I-2-a) are obtained:

(I-2-a)

Ex. No. V W X Y Z m.p.° C. I-2-a-2 H CH₃ CH₃ Cl H 266-269 I-2-a-3 H HCH₃ CH₃ CH₃ 213-214 I-2-a-4 H CH₃ Br CH₃ H 245 I-2-a-5 H CH₃ CH₃ Br H270 I-2-a-6 H CH₃ Cl CH₃ H 248-250 I-2-a-7 H CH₃ CH₃ CH₃ CH₃ 218

Example I-2-b-1

1.45 g (0.012 mol) of pivaolyl chloride are added dropwise to 2.88 g(0.01 mol) of the compound of Example I-2-a-1 and 1.2 g (0.012 mol) oftriethylamine in 30 ml of anhydrous methylene chloride, and the mixtureis stirred until the reaction has ended. This is followed by customarywork-up. Yield: 3.47 g, m.p.: 108° C.

Similarly to Example (I-2-b-1) and according to the general procedures,the following compounds of the formula (I-2-b) are obtained:

(I-2-b)

Ex. No. V W X Y Z R¹ m.p.° C. I-2-b-2 H H CH₃ CH₃ CH₃ i-C₃H₇ 106-107I-2-b-3 H CH₃ CH₃ CH₃ H i-C₃H₇ 115 I-2-b-4 H CH₃ CH₃ Cl H i-C₃H₇ 109-110I-2-b-5 H CH₃ Br CH₃ H i-C₃H₇  94 I-2-b-6 H CH₃ CH₃ Br H i-C₃H₇ 118I-2-b-7 H CH₃ Cl CH₃ H i-C₃H₇ 96-98 I-2-b-8 H CH₃ CH₃ CH₃ CH₃ i-C₃H₇ 115

Example I-2-c-1

1.64 g (0.012 mol) of isobutyl chloroformate are added dropwise to 2.88g (0.01 mol) of the compound of Example I-2-a-1 and 1.2 g (0.012 mol) oftriethylamine in 30 ml of anhydrous methylene chloride, and the mixtureis stirred until the reaction has ended. This is followed by customarywork-up. Yield: 3.8 g, m.p.: 107° C.

Similarly to Example (I-2-c-1) and according to the general preparationprocedures, the following compounds of the formula (I-2-c) are obtained:

(I-2-c)

Ex. No. V W X Y Z M R² m.p.° C. I-2-c-2 H H CH₃ CH₃ CH₃ O i-C₄H₉ 102-103I-2-c-3 H CH₃ CH₃ CH₃ H S i-C₃H₇ 105-106 I-2-c-4 H CH₃ CH₃ Cl H O i-C₄H₉143 I-2-c-5 H CH₃ Br CH₃ H O i-C₄H₉  89 I-2-c-6 H CH₃ CH₃ Br H O i-C₄H₉138 I-2-c-7 H CH₃ Cl CH₃ H O i-C₄H₉ 90-92 I-2-c-8 H CH₃ CH₃ CH₃ CH₃ Oi-C₄H₉  95

Example (I-2-a-2)

Similarly to Example I-2-a-1, but starting with the compound of Example(III-2), the compound

is obtained. m.p. 266-269° C.

Example (III-1)

10 g (0.057 mol) of the compound of Example (XXVI) and 11.3 g of2,4,6-trimethyl-phenyl-acetyl chloride are heated at 140° C. for 6 hoursand subsequently degassed.

Yield 18.1 g of an oil, mass spectrum (MS) (m/e): 334 (M+, 36%), 160(38%), 133 (100%).

Similarly to Example (III-1), and/or according to the generalpreparation procedures, the following compounds of the formula (III) areobtained:

Ex. No. V W X Y Z m.p.° C. III-2 H CH₃ CH₃ Cl H oil III-3 H H CH₃ CH₃CH₃ oil III-4 H CH₃ Br CH₃ H oil III-5 H CH₃ CH₃ Br H oil III-6 H CH₃ ClCH₃ H oil III-7 H CH₃ CH₃ CH₃ CH₃ oil

Example XXIV

At room temperature, 116.8 g (1.17 mol) of 3-oxa-cyclohexa-1-one (seeBull. Soc. Chim. Fr. (1970), (10), 3521-3) are added dropwise to amixture of 222.4 g (3.27 mol) of 25% strength ammonia solution, 75 g(1.4 mol) of ammonium chloride, 68.7 g (1.4 mol) of sodium cyanide and210 ml of water, and the mixture is stirred at 45° C. overnight.Extraction with methylene chloride gives 95.2 g (64% of theory) of thecompound depicted above which was used without any further purificationfor preparing the compounds of the formula XXV.

Example (XXVI)

At from 0 to −20° C., the mixture of 89.3 g (0.7 mol) of the compound ofExample (XXVIa) in 420 ml of ethanol is saturated with HCl. The mixtureis stirred at 0° C. for another hour and then allowed to warm to roomtemperature over a period of about 3 hours.

Excess HCl is removed under reduced pressure and the mixture is thenconcentrated. The residue is admixed with 400 ml of cold water andstirred for 1 hour. This mixture is extracted twice with methylenechloride, and the extract is dried and concentrated.

Yield 90 g, bp_(0.06)66° C.

Example (XXVIa)

At room temperature, 24.3 g (0.9 mol) of hydrocyanic acid are addeddropwise to 85.0 g (0.85 mol) of 3-oxa-cyclohexa-1-one (Bull. Soc. Chim.Fr. (1970) (10), 3521-3) and 0.72 ml of triethylamine, and the mixtureis stirred at room temperature for another 1.5 hours. The mixture isstabilized with 0.12 ml of o-phosphoric acid and degassed under waterpump vacuum.

Yield: 102 g (94% of theory).

USE EXAMPLES Example A

Myzus-Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by peachaphids (Myzus persicae) are treated by being dipped into the preparationof active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example the compounds of Preparation Examples(I-1-a-2), (I-1-a-3), (I-1-b-2) and (I-1-c-1) effected at an exemplaryconcentration of active compound of 0.1%, a kill of 100% after 6 days.

Example B

Nephotettix-Test

Solvent: 20 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryzae sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with the green rice leaf hoppers (Nephotettix cincticeps)while the seedlings are still moist.

After the desired period of time, the kill in % is determined. 100%means that all leaf hoppers have been killed; 0% means that none of theleaf hoppers have been killed.

In this test, for example the compounds of Preparation Examples(I-1-a-1), (I-1-a-2), (I-1-a-3), (I-1-b-1), (I-1-b-2), (I-1-b-3),(I-1-b4), (I-1-b-5) and (I-1-c-3) effected, at an exemplaryconcentration of active compound of 0.1%, a kill of 100% after 6 days.

Example C

Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example the compounds of Preparation Examples(I-1-a-1), (I-1-a-2), (I-1-a-3), (I-1-b-1), (I-1-b-2), (I-1-b-3),(I-1-b-4), (I-1-b-5) and (I-1-c-1) effected, at an exemplaryconcentration of active compound of 0.1%, a kill of 100% after 7 days.

Example D

Spodoptera frugiperda Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the owlet moth Spodoptera frugiperda)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example the compounds of Preparation Examples (I-1-b4)and (I-1-c-1) effected, at an exemplary concentration of active compoundof 0.1%, a kill of 100% after 7 days.

Example E

Tetranychus test (OP-resistent/dip treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by allstages of the greenhouse red spider mite Tetranychus urticae are dippedinto a preparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example the compounds of Preparation Examples(I-1-a-1), (I-1-b-1), (I-1-b-2) und (I-1-c-1) effected, at an exemplaryconcentration of active compound of 0.1%, a kill of 100% after 13 days.

What is claimed is:
 1. Compounds of the formula (I),

wherein V represents hydrogen, halogen, alkyl or alkoxy, W representshydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, alkoxy,halogenoalkyl, halogenoalkoxy, or represents unsubstituted orsubstituted phenyl, phenoxy, phenylthio, phenylalkoxy orphenylalkylthio, X represents halogen, alkyl, alkenyl, alkynyl, alkoxy,halogenoalkyl, halogenoalkoxy, cyano, nitro, or represents unsubstitutedor substituted phenyl, phenoxy, phenylthio, phenylalkyloxy orphenylalkylthio, Y represents hydrogen, halogen, alkyl, alkoxy,halogenoalkyl, halogenoalkoxy, cyano or nitro, Z represents hydrogen,halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano,nitro or represents unsubstituted or substituted phenoxy, phenylthio, 5-or 6-membered hetaryloxy, 5- or 6-membered hetarylthio, phenylalkyloxyor phenylalkylthio, or Y and Z together with the linking carbon atomsrepresent an unsubstituted or substituted cycle which is optionallyinterrupted by one or more heteroatoms, or W and Z together with thelinking carbon atoms represent an unsubstituted or substituted cyclewhich is optionally interrupted by one or more heteroatoms, Hetrepresents the group

wherein G represents hydrogen (a) or represents one of the groups

wherein E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents unsubstituted or halogen- or cyano-substituted alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl or representsunsubstituted or halogen-, alkyl- or alkoxy-substituted cycloalkyl orheterocyclyl or represents unsubstituted or substituted phenyl,phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² representsunsubstituted or halogen- or cyano-substituted alkyl, alkenyl,alkoxyalkyl or polyalkoxyalkyl or represents unsubstituted orsubstituted cycloalkyl, phenyl or benzyl, R³, R⁴ and R⁵ independently ofone another each represent unsubstituted or halogen-substituted alkyl,alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio orcycloalkylthio or represent unsubstituted or substituted phenyl, benzyl,phenoxy or phenylthio, R⁶ and R⁷ independently of one another eachrepresent hydrogen, or unsubstituted or halogen- or cyano-substitutedalkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, or representunsubstituted or substituted phenyl or benzyl, or together with thelinking N atom form an optionally oxygen- or sulphur-containing andoptionally substituted cycle.
 2. Compounds of the formula (I) accordingto claim 1, wherein V represents hydrogen, halogen, C₁-C₆-alkyl orC₁-C₆-alkoxy, W represents hydrogen, nitro, cyano, halogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy or represents unsubstituted or halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,phenylthio, phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio, X representshalogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano, nitro or representsunsubstituted or halogen-, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro- or cyano-substitutedphenyl, phenoxy, phenylthio, phenyl-C₁-C₄-alkoxy orphenyl-C₁-C₄-alkylthio, Y represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro,Z represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, hydroxyl, cyano, nitro orrepresents unsubstituted or halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenoxy, phenylthio, thiazolyloxy, pyridinyloxy, pyrimidyloxy,pyrazolyloxy, phenyl-C₁-C₄-alkyloxy or phenyl-C₁-C₄-alkylthio or Y and Ztogether with the linking carbon atoms represent unsubstituted orhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₅-alkanediyl or C₃-C₅-alkenediyl in which optionally one to threemembers may be replaced independently of one another by oxygen, sulphur,nitrogen or a carbonyl group, or W and Z together with the linkingcarbon atoms represent unsubstituted or halogen-, C₁-C₆-alkyl-,C₁-C₅-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₅-alkanediyl orC₃-C₅-alkenediyl, wherein one to three members may be replacedindependently of one another by oxygen, sulphur, nitrogen or a carbonylgroup, R¹ represents unsubstituted or halogen- or cyano-substitutedC₁-C₂₀-alkyl, C₂-C₂-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₈-alkylthio-C₁-C₈-alkyl or poly-C₁-C₈-alkoxy-C₁-C₈-alkyl orrepresents unsubstituted or halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxysubstituted C₃-C₈-cycloalkyl, wherein optionally one or two not directlyadjacent methylene groups are replaced by oxygen and/or sulphur, orrepresents unsubstituted or halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆alkoxy-, C₁-C₆-halogenoalkyl-, ₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulfonyl-substituted phenyl, orrepresents unsubstituted or halogen-, nitro-, cyano-, C₁-C₆-alkyl-,C₁-C₆alkoxy-, C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl, or represents unsubstituted or halogen- orC₁-C₆-alkyl-substituted 5- or 6-membered hetaryl having one or twoheteroatoms from the group consisting of oxygen, sulphur and nitrogen,or represents unsubstituted or halogen- or C₁-C₆-alkyl-substitutedphenoxy C₁-C₈-alkyl or represents unsubstituted or halogen-, amino- orC₁-C₆-alkyl-substituted 5-or 6-membered hetaryloxy-C₁-C₆-alkyl havingone or two heteroatoms from the group consisting of oxygen, sulphur andnitrogen, R² represents unsubstituted or halogen- or cyano-substitutedC₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₂-C₈-alkyl, or represents unsubstituted or halogen-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or representsunsubstituted or halogen-, cyano-, nitro-, C₁-C₆alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substituted, phenyl orbenzyl, R³ represents unsubstituted or halogen-substituted C₁-C₈-alkylor represents unsubstituted or halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano- or nitro-substitutedphenyl or benzyl, R⁴ and R⁵ independently of one another each representunsubstituted or halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio orC₃-C₈alkenylthio or represent unsubstituted or halogen-, nitro-, cyano-,C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-halogenoalkylthio-, C₁-C₄-alkyl- orC₁-C₄-halogenoalkyl-substituted phenyl, phenoxy or phenylthio, and R⁶and R⁷ independently of one another each represent hydrogen, representunsubstituted or halogen- or cyano-substituted C₁-C₈-alkyl,C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₁-C₈-alkenyl orC₁-C₈-alkoxy-C₂-C₈-alkyl, represent unsubstituted or halogen-,C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- or C₁-C₈-alkoxy-substituted phenyl orbenzyl or together represent an unsubstituted or C₁-C₆-alkyl-substitutedC₃-C₆-alkylene radical, wherein optionally one methylene group isreplaced by oxygen or sulphur.
 3. Compounds of the formula (I) accordingto claim 1, wherein V represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl or C₁-C₄-alkoxy, W represents hydrogen, nitro, cyano,fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy or represents unsubstituted orfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenoxy or benzyloxy, X represents fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano, nitro or represents unsubstituted or fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy orbenzyloxy, Y represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano or nitro, Z represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,hydroxyl, cyano, nitro or represents unsubstituted or fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenoxy or benzyloxyor Y and Z together with the linking carbon atoms representunsubstituted or fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₂-halogenoalkyl-substituted C₃-C₄-alkanediyl orC₃-C₄-alkenediyl, wherein optionally one or two not directly adjacentmembers may be replaced independently of one another by oxygen, sulphuror nitrogen, or W and Z together with the linking carbon atoms representunsubstituted or fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₂-halogenoalkyl-substituted C₃-C₄-alkanediyl orC₃-C₄-alkenediyl, wherein one or two not directly adjacent members maybe replaced independently of one another by oxygen, sulphur or nitrogen,R¹ represents unsubstituted or fluorine- or chlorine-substitutedC₁-C₁₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl or poly-C₁-C₆-alkoxy-C₁-C₆-alkyl orrepresents unsubstituted or fluorine-, chlorine-, C₁-C₅-alkyl- or orC₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl, wherein optionally one or twonot directly adjacent methylene groups are replaced by oxygen and/orsulphur, or represents unsubstituted or fluorine-, chlorine-, bromine-,cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- or C₁-C₄-alkylsulphonylsubstituted phenyl, or represents optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl- orC₁-C₃-halogenoalkoxy-substituted phenyl-C₁-C₄-alkyl, or representsunsubstituted or fluorine-, chlorine-, bromine- orC₁-C₄-alkyl-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl,furanyl or thienyl, or represents unsubstituted or fluorine-, chlorine-,bromine-, or C₁-C₄-alkyl-substituted phenoxy-C₁-C₅-alkyl or representsunsubstituted or fluorine-, chlorine-, bromine- amino- orC₁-C₄-alkyl-substituted pyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkylor thiazolyloxy-C₁-C₅-alkyl, R² represents unsubstituted or fluorine- orchlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl, representsunsubstituted or fluorine-, chlorine-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or represents unsubstituted orfluorine, chlorine, bromine-, cyano, nitro, C₁-C₄-alkyl-, C₁-C₃-alkoxy-,C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substituted phenyl orbenzyl, R³ represents unsubstituted or fluorine- or chlorine-substitutedC₁-C₆-alkyl or represents unsubstituted or fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy, C₁-C₂-halogenoalkoxy-,C₁-C₂-halogenoalkyl-, cyano- or nitro-substituted phenyl or benzyl, R⁴and R⁵ independently of one another each represent unsubstituted orfluorine- or chlorine-substituted C₁-C₆-alkyl-, C₁-C4-alkoxy-,C₁-C₆-alkylamino-, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio orC₃-C₄-alkenylthio or represent unsubstituted or fluorine-, chlorine-,bromine-, nitro-, cyano-, C₁-C₃-alkoxy-, C₁-C₃-halogenoalkoxy-,C₁-C₃-alkylthio-, C₁-C₃-halogenoalkylthio-, C₁-C₃-alkyl orC₁-C₃-halogenoalkyl-substituted phenyl, phenoxy or phenylthio, and R⁶and R⁷ independently of one another each represent hydrogen, representunsubstituted or fluorine- or chlorine-substituted C₁-C₆-alkyl,C₃C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl, represent unsubstituted or fluorine-,chlorine-, bromine-, C₁-C₅-halogenoalkyl-, C₁-C₅-alkyl- or C₁-C₅-alkoxysubstituted phenyl or benzyl, or together represent an unsubstituted orC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical, wherein optionally onemethylene group is replaced by oxygen or sulphur.
 4. Compounds of theformula (I) according to claim 1, wherein V represents hydrogen,fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl,tert-butyl, methoxy, ethoxy, propoxy or iso-propoxy, W representshydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl,propyl, n-butyl, iso-propyl, iso-butyl, methoxy, ethoxy, propoxy,iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, phenylor benzyloxy, X represents fluorine, chlorine, bromine, methyl, ethyl,propyl, butyl, iso-butyl, iso-propyl, methoxy, ethoxy, propoxy,iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano,nitro, phenyl or benzyloxy, Y represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl,tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano or nitro, Z representshydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl,iso-butyl, iso-propyl, tert-butyl, methoxy, ethoxy, propoxy,iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyanoor nitro or Y and Z together with the linking carbon atoms representunsubstituted or fluorine-, chlorine-, methyl-, ethyl-propyl-,iso-propyl-, methoxy-, ethoxy-, propoxy-, iso-propoxy- ortrifluoromethyl-substituted C₃-C₄-alkanediyl, wherein optionally two notdirectly adjacent members are replaced by oxygen or W and Z togetherwith the linking carbon atoms represent unsubstituted or fluorine-,chlorine-, methyl-, ethyl-, propyl-, iso-propyl-, methoxy-, ethoxy-,propoxy-, iso-propoxy- or trifluoromethyl-substituted C₃-C₄alkanediyl,wherein optionally two not directly adjacent members are replaced byoxygen, R¹ represents unsubstituted or chlorine- or fluorine-substitutedC₁-C₁₄-alkyl, C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl,C₁-C₄-alkylthio-C₁-C₆-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or representsunsubstituted or fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,i-propyl-, n-butyl-, i-butyl-, tert-butyl, methoxy-, ethoxy-, n-propoxy-or iso-propoxy-substituted C₃-C₆-cycloalkyl, wherein optionally one ortwo not directly adjacent methylene groups are replaced by oxygen and/orsulphur, or represents unsubstituted or fluorine-, chlorine-, bromine-,cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-,ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-,methylsulphonyl- or ethylsulphonyl-substituted phenyl, or representsunsubstituted or fluorine-, chlorine-, bromine-, methyl-, ethyl-,n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted benzyl, or represents substituted orfluorine-, chlorine-, bromine-, methyl- or ethyl-substituted furanyl,thienyl or pyridyl, or represents unsubstituted or fluorine-, chlorine-,methyl- or ethyl-substituted phenoxy-C₁-C₄-alkyl or representsunsubstituted or fluorine-, chlorine-, amino-, methyl- orethyl-substituted pyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl orthiazolyloxy-C₁-C₄-alkyl, R² represents unsubstituted or fluorine- orchlorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₂-C₆-alkyl or poly-C₁-C₄-alkoxy-C₂-C₆-alkyl, or representsunsubstituted or fluorine-, chlorine-, methyl-, ethyl-, n-propyl,iso-propyl- or methoxy-substituted C₃-C₆-cycloalkyl, or representsunsubstituted or fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-,n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl or benzyl, R³ representsunsubstituted or fluorine- or chlorine-substituted methyl, ethyl,propyl, iso-propyl, n-butyl, tert-butyl, or represents unsubstituted orfluorine-, chlorine-, bromine-, methyl-, ethyl-, iso-propyl-,tert-butyl-, methoxy-, ethoxy-, iso-propoxy-, trifluoromethyl-,trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴ andR⁵ independently of one another each represent unsubstituted orfluorine- or chlorine-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino or C₁-C₄-alkylthio or representunsubstituted or fluorine-, chlorine-, bromine-, nitro-, cyano-,methyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substitutedphenyl, phenoxy or phenylthio, and R⁶ and R⁷ independently of oneanother represent hydrogen, represent unsubstituted or fluorine- orchlorine-substituted C₁-C₄-alkyl, C₃-C₆cycloalkyl, C₁-C₄-alkoxy,C₃-C₄-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, represent unsubstituted orfluorine-, chlorine-, bromine-, methyl-, methoxy- ortrifluoromethyl-substituted phenyl or benzyl, or together represent anunsubstituted or methyl- or ethyl-substituted C₅-C₆-alkylene radical,wherein optionally one methylene group is replaced by oxygen or sulphur.5. A pesticidal or herbicidal composition comprising compounds of theformula (I) according to claim 1 and an acceptable diluent.
 6. A methodfor controlling pests and weeds, comprising the step of applying atleast one compound of the formula (I) according to claim 1 on pests,weeds, pest habitat, and/or weed habitat.
 7. A process for preparingcompounds of the formula (I) according to claim 1, wherein compounds ofthe formula (I-1-a)

wherein V, W, X, Y and Z are each as defined in claim 1 are obtainedwhen compounds of the formula (II)

wherein V, W, X, Y and Z are each as defined above, and R⁸ representsalkyl, are intramolecularly condensed in the presence of a diluent andin the presence of a base.
 8. A process for preparing pesticides andherbicides, comprising the step of mixing compounds of the formula (I)according to claim 1, with an ingredient selected from the grougconsisting of extenders, surfactants and mixtures thereof.